What’s Worse than a Difficult Conversation? Avoiding One.

As a leader, how can you confront the truth about a situation without fearing rejection, or disagree with someone clearly and cleanly without obsessing about causing offense?

I have been an executive with major corporations, including PepsiCo, Shell, and BBC Worldwide, as well as a change consultant. I’ve learned that in leadership roles the most important work often happens in the least comfortable spaces. Handled well, risky and confrontational conversations — especially those that surface awkward facts or get to the source of organizational tensions — can improve how we relate to each other, help organizations get a better grip on reality, and enable leaders to make better decisions.

Yet while we tell ourselves that these conversations are tough because we don’t want to upset the other person, usually the squirmy feeling we’re experiencing has less to do with our counterpart and more to do with our own unconscious anxiety about not being able to handle the conversation well. Overcoming these anxieties and having the tough conversations anyway is one of a top leader’s most difficult challenges — critically needed yet chronically hard to do.

For advice on how to handle it better, I turned to executives who have conversations on some of the trickiest topics in an organization: trust on teams, organizational restructuring, and addressing underperformance. By definition, these kinds of conversations require you to get out of your comfort zone. You may even feel like you’re betraying former loyalties to past products, old ways of working, personal affiliations, or previous professional identities.

I found that four elements make the difference. First and foremost, in my own experience and with the executives I’ve talked to, is a shift in mindset from seeing difficult conversations as a hurdle to seeing them as a resource. Difficult conversations can actually strengthen personal bonds if you handle them well. For example, one leader I interviewed* was able to see a difficult conversation as a route to building trust in his team:

I think you have to be very wary of the indirect comments and conversations that are going around in a meeting. You might see or sense a couple of people who are threatened by the restructure or are a little unhappy about one element. I had an incident recently where I had to say, “Look, I sense that a couple of us here feel threatened by this, so let’s actually have this out as a team,” and [I’m using that conversation to] build the levels of trust and openness among my team.

Second, leaders must have the skill of regulating their emotional responses in difficult conversations. Now, too many leaders understand this to mean that they have to take emotions out of it completely. That’s not realistic, and burying feelings can be as destructive as letting them all spill out. Instead, skilled leaders use their emotions in a constructive way. One leader I talked to as part of this project was working with an external coach to help him get better at selling a major change. Here’s how he describes being in charge of his emotions during a tense conversation with that coach:

Emotionally, I was not enthused, but something inside me was saying, well, he might have a point. And he was an external coach, so there was clearly no hidden agenda on his side. So I somehow forced myself to swallow my pride and my anger and discuss with him how he would go about achieving the goal I had, so that my CFO would be more likely to build and own the solution.

Third, leaders need the ability to tell it as it is without waffle yet with compassion, balancing advocacy with inquiry. Here’s a leader bringing direct yet empathetic straight-talking into a restructuring:

I remember having some of the toughest conversations around the restructure. For instance, with some of the countries we’d be on a videoconference and they would say, “Look, we want to form a different brand,” or they’d say, “We want to do our own logo,” just things like that, and I was having to be quite brutal, saying, “Just so you’re clear, this is nonnegotiable, and this is not your call.” I know it sounds horrid, but I did it with a smile on my face.

Finally, the leader needs to be able to create psychological safety for the conversation. Take this leader, who used appreciation and a well-known dialogue tool to make it okay for his brand-new team to have a risky conversation with him:

I arranged for a couple of days off-site where I asked them to help me understand the business. I said, “You know all about it, and you’ve grown up in it, and you’ve got hundreds of years of experience between you. I’ve got none. I want you to help me understand what’s going well and what’s not going so well.” I used the de Bono Six Thinking Hats as a tool to try to let their emotions out and legitimize them, doing some black cap [critical] thinking, just so I could get beyond the, “Oh, it’s nice to have you here,” and all the politeness.

For all those involved as leaders in confronting truth and enabling others to do so, the essential message is simple: Safety is perilous, and difficulty is strengthening.